Tallinn, Estonia has three layers. The first is bonny Tallinn, with its perfect medieval UNESCO old town. The second is post-Soviet Tallinn, a grey decaying relic of the former occupation. The third is hipster Tallinn, drinking craft beer and spray painting the town. To understand the city, you really should explore all three.
The first fortress was built in Tallinn in 1050. The city experienced successive waves of occupation from the Germans, the Swedes, the Russians, the Germans (again) and (yet again) the Russians, before finally achieving their independence in 1990. Tallinn was fortunate because it was never fully pillaged or razed, and while it got damaged in WWII, it wasn’t destroyed. So, what you’ll find there is a complex layer cake of history with a very pretty UNESCO heritage frosting on top.
Top Historic Spots: Wandering around Old Town, killer views at the Kohtuotsa viewing platform, touring the Bastion Passages, exploring seafaring history at the Seaplane Harbor museum and finding royalty at Kadriorg Park.
Old Town is a pretty base layer, which is then topped off by a decaying hulk of Soviet relics. After fifty years of Soviet occupation, Tallinn has a lot of urbex spots and disused Soviet hardware. Touring these facilities is the best way to get an education on the occupation and get an urbex fix at the same time.
Top Soviet sites: Go to the top of Teletorn TV tower, crawl around Linnahall and tour the KGB Museum.
Our final layer of Tallinn is the modern one. Hipster Tallinn sits on top of Soviet Tallinn like a colorful coating of fresh (spray) paint. The Old Town might be old, but the neighborhoods surrounding it are very modern. If you only visit the historical sights, then you will miss learning about how Estonia is re-inventing itself as a modern economy.
Top Hipster sites: Finding street art and galleries at Telliskivi Creative City, Balti Jaam market, Kumu Museum and craft beer at Pudel or Hell Hunt.
This article is excerpted. You can find the full article with more suggestions and photos at Wayfaring Views.